Water → tert-Butyl 4-(hydroxymethyl)phenethylcarbamate

HRID 1668378Notes

Reaction equation

HRID 1668378 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[CH:21]=[CH:20][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67360059Ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate

Product 1

HCID 22337080tert-Butyl 4-(hydroxymethyl)phenethylcarbamateYield 110.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-{2-[(tert-butoxycarbonyl)amino]ethyl}benzoate (4 g) in tetrahydrofuran (30 ml) was added lithium aluminum hydride (0.82 g), and the mixture was stirred at 0° C. for 30 min. Water (3.6 ml) and 1N aqueous sodium hydroxide solution (1 ml) were added to quench the reaction, and the precipitate was filtered off. The filtrate was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (3.8 g) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationthe precipitate was filtered off
  4. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de4567951caa4cb3ba3d6ee498c63e9d
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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